I’m so excited to bring you this very special imaginary talk, where we’re diving into a book that’s all about embracing your true worth—Worthy by Jamie Kern Lima. This book is not just a guide but a journey, and today, we have the incredible opportunity to explore its themes with some of the most inspiring women in business.
Joining Jamie are women who have not only built successful companies but have also redefined what it means to be a female entrepreneur. We have Sara Blakely, the visionary behind Spanx, who turned a simple idea into a billion-dollar empire; Sophia Amoruso, the bold founder of Nasty Gal and author of #GIRLBOSS, who’s paved the way for so many with her fearless approach; Tiffany Pham, the founder of Mogul, who’s been a champion for women’s empowerment in the tech world; and Kendra Scott, whose innovative designs and philanthropic spirit have made her a beloved figure in the fashion industry.
In this conversation, we’ll explore how these remarkable women have navigated their own journeys of self-worth, resilience, and innovation. We’ll hear about the setbacks they’ve faced, the confidence they’ve built, and the ways they’ve given back to their communities. While this conversation is imaginary, the insights, experiences, and wisdom shared are very real and will leave you feeling inspired and empowered. So, let’s dive in and discover together what it truly means to be Worthy.
Embracing Authenticity in Business
Nick Sasaki: Welcome everyone. Today, we’re starting with a discussion on authenticity in business, a value each of you holds dear. Let’s explore how embracing your true self has shaped your journey and success.
Jamie Kern Lima: Authenticity has always been at the core of my journey. When I started IT Cosmetics, I was determined to create products that addressed real beauty concerns. I faced countless rejections from people who didn’t believe in my vision. But I knew that my personal struggles with skin issues gave me a unique perspective. By staying true to my story and understanding my customers’ needs, I built a brand that resonated with millions of people. Authenticity isn’t just about being honest with others; it’s about being honest with yourself and what you stand for.
Sara Blakely: I completely agree, Jamie. When I created Spanx, I was solving a problem that I personally experienced. I wanted to feel more confident in white pants without the discomfort of traditional undergarments. By embracing that personal struggle and talking openly about it, I was able to connect with other women who felt the same way. In business, authenticity has been my guiding principle. It’s easy to get lost in what you think others expect of you, but staying true to yourself and your mission is what builds a lasting brand.
Sophia Amoruso: For me, authenticity was about embracing my unconventional path. I didn’t have a traditional business background when I started Nasty Gal, and I wasn’t afraid to share that. I used my unique experiences to build a brand that stood out in the fashion industry. People connected with Nasty Gal because it was different and unapologetically authentic. Being real about who you are, and where you come from, can set you apart in a crowded market.
Tiffany Pham: Authenticity is also about owning your story, especially when it’s not the typical success narrative. When I started Mogul, I was often the only woman of color in the room, which made me feel like I had to work even harder to prove myself. Instead of hiding those challenges, I chose to embrace them and share my story with others. This allowed me to connect with my audience on a deeper level. They saw themselves in my journey, which created a strong bond of trust and loyalty. Authenticity isn’t just a nice-to-have; it’s a necessity for anyone who wants to make a real impact.
Kendra Scott: I’ve found that authenticity in business also means being transparent with your customers and team. When I started my jewelry line, I was a young mother working out of a spare bedroom. I shared that part of my life with my customers, and it resonated with them. They weren’t just buying jewelry; they were supporting a mom trying to balance her dreams with her family life. Authenticity helped me build a community around my brand, where customers felt like they were part of my journey.
Nick Sasaki: Each of you has shown that authenticity is not just a principle but a powerful tool for building strong connections with your audience. Whether it’s through sharing personal struggles, embracing your unique path, or being transparent with your customers, your authenticity has set you apart in the industry. This genuine approach has fostered trust, loyalty, and a sense of community around your brands. Let’s continue exploring how these values have influenced other aspects of your journeys in our next topic.
Overcoming Rejection and Setbacks
Nick Sasaki: Let's move on to our next topic—overcoming rejection and setbacks. Each of you has faced significant challenges in your careers, and I’m interested in hearing how you navigated those tough times and turned them into opportunities.
Jamie Kern Lima: Rejection was a constant companion in the early days of IT Cosmetics. I was told ‘no’ so many times by potential investors and retailers who didn’t believe in the brand or the mission behind it. Each rejection felt like a blow, but I knew I had to keep pushing forward. The turning point for me was realizing that every ‘no’ brought me closer to the right ‘yes.’ I used the rejections as fuel to refine my pitch and strengthen my resolve. It wasn’t easy, but I kept my focus on the bigger picture—helping people feel confident in their skin.
Sara Blakely: I can definitely relate to that, Jamie. When I was starting Spanx, I faced numerous setbacks, especially in the beginning. I had no background in business or fashion, and I heard a lot of skepticism from people who thought my idea wouldn’t work. But those setbacks didn’t deter me; they motivated me. I remember driving around in my car, selling Spanx out of the trunk because no one else believed in the product. The key for me was to keep my sense of humor and not take rejection personally. It was about learning from every experience and staying persistent, no matter how tough things got.
Sophia Amoruso: Rejection and setbacks were part of my journey as well, especially when I transitioned from Nasty Gal to other ventures. There were times when things didn’t go as planned, and I had to pivot quickly. The biggest lesson I learned was not to let setbacks define me. Instead, I used them as opportunities to reinvent myself and explore new paths. I think it’s important to remember that failure is not the opposite of success; it’s part of the process. Each setback gave me the resilience to keep moving forward and the wisdom to make better decisions.
Tiffany Pham: My experience with setbacks was similar. When I started Mogul, I encountered a lot of resistance, particularly because I was a young woman of color trying to break into the tech space. There were many doors that didn’t open for me, and it was frustrating at times. But I learned to see setbacks as stepping stones. They taught me to be resourceful and to find new ways to achieve my goals. One thing that helped me was building a support network of mentors and peers who believed in my vision. Their encouragement kept me going when things were tough.
Kendra Scott: Setbacks have played a huge role in shaping my journey as well. When I launched my jewelry business, I faced financial challenges and the pressure of balancing work with family life. There were moments when I felt like giving up, especially when the business wasn’t growing as fast as I’d hoped. But I realized that setbacks are a natural part of entrepreneurship. They test your commitment and push you to find creative solutions. For me, it was about staying focused on my passion for design and the belief that my work could bring joy to others. That belief kept me moving forward, even in the face of adversity.
Nick Sasaki: Your stories highlight the resilience and determination needed to navigate rejection and setbacks in the business world. Each of you turned these challenges into catalysts for growth, showing that setbacks can often be the most powerful motivators. As we continue, let’s delve into how you’ve built and maintained the confidence to persevere through these tough times in our next topic.
Building and Maintaining Confidence
Nick Sasaki: For our next discussion, let’s focus on the theme of confidence. Building and maintaining confidence is crucial, especially in the face of challenges and uncertainty. How have you cultivated and sustained your confidence throughout your entrepreneurial journeys?
Jamie Kern Lima: Confidence was something I had to build over time, especially after facing so many rejections. In the beginning, it wasn’t easy. I questioned myself a lot, wondering if I was really capable of achieving my goals. But I realized that confidence isn’t about always feeling sure of yourself; it’s about believing in your purpose and mission, even when doubts creep in. One thing that helped me was surrounding myself with people who believed in me, even when I didn’t fully believe in myself. Their support was invaluable. I also focused on small wins—celebrating each step forward, no matter how minor. These moments of progress helped reinforce my confidence over time.
Sara Blakely: Confidence for me has always been tied to my willingness to take risks. I didn’t know the first thing about the fashion industry when I started Spanx, but I was confident in my ability to figure things out as I went along. I’ve always believed that taking action, even when you’re scared, is the key to building confidence. The more risks I took, the more I realized that failure wasn’t something to be feared; it was something to learn from. That shift in mindset made a huge difference. Confidence isn’t about never failing; it’s about knowing that you can handle whatever comes your way.
Sophia Amoruso: I’ve found that confidence often comes from being unapologetically yourself. When I started Nasty Gal, I didn’t have the same credentials or background as others in the industry, but I had a clear vision and a unique voice. I leaned into that, even when others doubted me. There were definitely times when my confidence wavered, but I learned to trust my instincts and stay true to my vision. Confidence, for me, is about owning your story and being proud of where you’ve come from, regardless of what others might think.
Tiffany Pham: Confidence has been something I’ve had to actively cultivate, especially as a woman in tech. It wasn’t always easy to walk into rooms where I was often the only woman or person of color and feel like I belonged. But I realized that confidence comes from preparation and knowing your worth. I worked hard to build my knowledge and skills, so when I walked into those rooms, I knew I had something valuable to offer. I also focused on self-care and mental wellness, understanding that taking care of myself was essential to maintaining my confidence over the long haul.
Kendra Scott: For me, confidence has been about finding balance and knowing when to trust myself. As a mom and a business owner, there were times when I felt pulled in so many different directions that it was hard to feel confident in any one area. But I learned that confidence comes from being true to yourself and setting boundaries. It’s about recognizing that you can’t do everything perfectly, and that’s okay. I also made it a point to build a supportive team that I could rely on, which allowed me to focus on my strengths and build confidence in what I was doing.
Nick Sasaki: Your insights into building and maintaining confidence reveal that it’s a dynamic process—one that involves taking risks, trusting your instincts, and surrounding yourself with the right support. Confidence isn’t about never doubting yourself; it’s about having the courage to move forward despite those doubts. As we continue, let’s explore how each of you has used innovation and creativity to solve problems and drive your businesses forward in our next topic.
Leveraging Innovation and Creativity
Nick Sasaki: Now, let’s dive into how innovation and creativity have played a role in your success. Each of you has built your business on unique ideas that disrupted the market. How have you harnessed innovation and creativity to solve problems and propel your ventures forward?
Jamie Kern Lima: Innovation was at the heart of IT Cosmetics from the very beginning. The beauty industry is highly competitive, and I knew I had to offer something different. I didn’t just want to create another makeup line; I wanted to solve real problems that women, including myself, were facing. Our innovative products, like the CC Cream that offers full coverage with skincare benefits, came from listening to what customers needed and thinking outside the box. Creativity wasn’t just in product development but also in how we connected with our customers. We used real women of all ages, sizes, and skin types in our marketing, which was groundbreaking at the time and helped us stand out in a crowded market.
Sara Blakely: For Spanx, innovation was born out of necessity. I had a problem that needed solving—how to make white pants look better without visible panty lines—and I couldn’t find a product that worked. So, I invented one. But innovation didn’t stop there. I had to be creative in getting the product to market since I didn’t have traditional resources or industry connections. From cold-calling hosiery mills to personally pitching the product to Neiman Marcus, I found creative solutions to every obstacle. Creativity is about not letting conventional thinking limit your possibilities. It’s about seeing opportunities where others see challenges.
Sophia Amoruso: Nasty Gal started as an eBay store selling vintage clothes, and the creativity was in how we presented those clothes. We created a unique brand identity that was edgy, bold, and spoke directly to our audience in a way that no one else was doing at the time. Our styling, photography, and even the language we used in product descriptions were all part of that creative approach. As we grew, innovation came into play by leveraging social media before it became the norm, which allowed us to build a strong, loyal community around the brand. Being innovative isn’t just about the products you create; it’s also about how you connect with your audience and build a brand that resonates with them.
Tiffany Pham: Innovation for Mogul was about creating a platform that didn’t exist before—a space for women to connect, share, and grow professionally. The idea was innovative, but so was the way we built and scaled the platform. We used data-driven approaches to understand our users’ needs and continuously adapted the platform to meet those needs. Creativity was also crucial in how we marketed Mogul. We didn’t have the big budgets of some competitors, so we had to be resourceful and creative in getting the word out. This included leveraging partnerships, grassroots marketing, and building a strong narrative around our mission. Innovation and creativity are about finding new ways to solve problems and deliver value to your audience.
Kendra Scott: For me, innovation and creativity have been integral from day one. When I started Kendra Scott Jewelry, I was determined to create beautiful, high-quality pieces that were also accessible. The innovation was in the design and production process—how we could make luxury jewelry at an affordable price point without compromising on quality. Creativity also extended to how we engaged with our customers, offering a unique in-store experience that made them feel part of our community. Our Color Bar™, where customers can customize their own pieces, is a perfect example of blending creativity with innovation to offer something truly unique. Creativity isn’t just about the end product; it’s about every aspect of the business, from design to customer experience.
Nick Sasaki: Your experiences highlight how innovation and creativity are not just tools for product development but are woven into every aspect of your business strategies. By thinking outside the box and finding creative solutions to challenges, you’ve each been able to disrupt your industries and create lasting impact. Next, let’s turn our attention to the importance of giving back and how philanthropy has influenced your careers and businesses.
The Importance of Giving Back and Philanthropy
Nick Sasaki: As we wrap up our discussion, let’s focus on the role of philanthropy and giving back in your journeys. Each of you has made significant contributions to various causes. How has giving back influenced your careers and the direction of your businesses?
Jamie Kern Lima: Giving back has been an integral part of my journey. When I started IT Cosmetics, I was deeply aware of the impact that beauty standards can have on a person’s self-esteem. As the company grew, I felt a responsibility to use our platform to do more than just sell products. We partnered with organizations that support women facing cancer and survivors of domestic abuse, providing them with beauty products to help restore their confidence. Philanthropy has allowed me to align my business with my personal values, making the success of IT Cosmetics even more meaningful. It’s about making a difference and knowing that our efforts can positively impact others’ lives.
Sara Blakely: Philanthropy has always been a core value for me and for Spanx. When I first started making money, I set aside a portion of my earnings to help women entrepreneurs through microloans. I’ve always believed that when you achieve success, it’s important to lift others up along the way. That’s why I created the Sara Blakely Foundation, which focuses on empowering women and girls around the world. Giving back has not only enriched my life but has also given Spanx a deeper purpose beyond just selling products. It’s a reminder that our success can be a vehicle for positive change in the world.
Sophia Amoruso: For me, giving back has taken on different forms throughout my career. With Nasty Gal, I supported various causes that aligned with the brand’s values, from promoting body positivity to supporting women in the arts. Now, with Girlboss, I’m focused on creating resources and opportunities for women entrepreneurs. Philanthropy, for me, is about more than just writing a check; it’s about using my platform to create lasting change and provide tools for the next generation of women leaders. It’s deeply fulfilling to know that my work can inspire and empower others, and it’s shaped how I approach both my business and personal life.
Tiffany Pham: Philanthropy is at the very heart of Mogul. Our mission is to provide women with the tools and resources they need to succeed, and we’ve built our platform around that goal. We’ve partnered with numerous organizations to provide scholarships, mentorships, and career opportunities for women around the world. Giving back isn’t just an afterthought; it’s embedded in everything we do. I’ve seen firsthand how giving others the support they need can transform lives, and that drives me to continue finding ways to give back. It’s incredibly rewarding to see the impact we can have, and it fuels my passion for what we’re building at Mogul.
Kendra Scott: From the beginning, giving back has been a pillar of my business. When I started Kendra Scott Jewelry, I made a commitment that philanthropy would be a cornerstone of the company. We’ve donated millions of dollars to various causes, including education, health, and empowering women and children. One of our core initiatives is the Kendra Cares Program, where we bring the Color Bar™ experience to pediatric hospitals across the country. For me, philanthropy is about creating a legacy that goes beyond jewelry—it’s about leaving the world a better place than I found it. Knowing that my business can make a positive impact on so many lives is one of the most fulfilling aspects of my career.
Nick Sasaki: Your commitment to philanthropy and giving back is inspiring and underscores the impact that successful businesses can have on the world. Each of you has shown that true success is not just about personal achievement but about using your resources and influence to uplift others and make meaningful contributions to society. It’s clear that giving back has not only enriched your personal lives but has also infused your businesses with a deeper sense of purpose. Thank you all for sharing your insights and experiences today. Your stories are a testament to the power of resilience, innovation, and generosity in building not just successful companies, but also a better world.
Short Bios:
Jamie Kern Lima is the founder of IT Cosmetics and author of Worthy. She built her billion-dollar beauty brand from her living room and became the first female CEO in L'Oréal's history. Jamie is known for her resilience and authenticity, inspiring women to embrace their true worth.
Sara Blakely is the founder of Spanx, a leading shapewear brand that revolutionized the fashion industry. Starting with just $5,000 in savings, Sara grew Spanx into a billion-dollar company. She is celebrated for her innovative spirit and commitment to empowering women entrepreneurs.
Sophia Amoruso is the founder of Nasty Gal and author of #GIRLBOSS. She turned a small eBay store into a multi-million dollar fashion brand and has since become a voice for female empowerment through her work with Girlboss, a platform that supports women in business.
Tiffany Pham is the founder and CEO of Mogul, a global platform that provides resources and opportunities for women. She’s recognized as a leader in tech and women’s empowerment, using her platform to champion diversity and inclusion in the workplace.
Kendra Scott is the founder of Kendra Scott Jewelry, a brand known for its customizable designs and accessible luxury. Beyond business, Kendra is dedicated to philanthropy, supporting causes that empower women and children. Her innovative approach to retail has made her a beloved figure in the fashion industry.
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